Selective C-H bond activation by a supramolecular host-guest assembly

Angewandte Chemie - International Edition

Volumn 43, Issue 8, 2004, Pages 963-966

  Leung, Dennis H ^a   Fiedler, Dorothea ^a   Bergman, Robert G ^a   Raymond, Kenneth N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

C H activation; Diastereoselectivity; Gallium; Host guest systems; Iridium; Supramolecular chemistry

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL BONDS; IRIDIUM COMPOUNDS;

CHIRALS; IRIDIUM COMPLEX; LIGANDS;

SUPRAMOLECULAR CHEMISTRY;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; HYDROGEN BOND; PARTICLE SIZE; SUPRAMOLECULAR CHEMISTRY;

EID: 1642332752     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352772     Document Type: Article

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30. Yields ranging from 40-60% were obtained in these aldehyde activation reactions. At this temperature, some decomposition of the iridium metal complex to intractable products is observed for both the free and encapsulated species. Specific experimental yields are presented in the Supporting Information.
31. This selectivity is due to differences in shape and size rather than hydrophobicity of the substrate. Both 10 and 12 have the same hydrophobicity value as determined by an octanol/water partition experiment, but only 10 is activated by the encapsulated iridium host-guest complex.
32. CAChe MM2 force field molecular mechanics calculations could not detect a substantial difference in substrate binding selectivity. More sophisticated calculations have not yet been undertaken.